The Dark I Know Well
by CupcakeBatter
Summary: There's a price to pay for acceptance on the Upper East Side, she knows that now and she's not willing to pay it. / Jenny-centric with a lot of Jenny/Chuck friendship and some Jenny/Nate thrown in there as well.


There's good, there's bad and there's really fucking awful. Getting caught drunk off your ass with Chuck Bass and some sketchy looking friends of his (who was she kidding, at least one of them deals drugs) by her father and her brand new stepmother falls into the latter category.

The punishment does not fit the crime.

Her father has her on lockdown, judging her "irresponsible" behavior the way he judges her every move that reminds him, even remotely, that she is not growing up the way he did, somewhere in small town New Jersey.

She accepts his disappointed speeches, can deal with the lectures about the dangers of drinking, but when he suggests she see a therapist, she laughs.

It's not a bitter laugh, not even an exasperated one but Rufus' reaction is all the same. How dare she laugh at such a serious matter? How dare she put her future at risk? (And mostly: How dare you jeopardize the reputation of Lily van der Woodsen-Bass-Humphrey? How dare you make me look like a bad parent in front of my new wife?)

"Who are you?" he asks, and it sounds like an accusation.

She thinks it's a loaded question.

...

How did she get so messed up?

She has no friends.

She had Dan, but he looks at her like he doesn't recognize her now. Eric has long stopped being her friend, tired of putting up with her. Vanessa, the only girl she was ever truly friends with, she lost over a boy.

She remembers being friends with Nate. She remembers nights spent wandering the city, sharing secrets and smiles. For a while, their friendship seemed like a sure thing to her. It was easy, effortless. Teasing him relentlessly about his obsession with his hair and letting him make fun of her for her weak skills at arm wrestling in return, came naturally.

Then things changed. Girl meets bad boy photographer, Boy gets protective and frustration leads to a kiss that should not feel as right as it does. (This time, he knows she's not Serena and he doesn't need her to be.)

Their happiness lasts less than ten hours. Being together seemed effortless when no one else was around but the bitter reality of family brunch with her brother and father the next morning puts a damper on things.

The fashion show. The big reveal. The day she sees her brother throw a punch because of her for the second time.

Days spent in agony over why he left without saying goodbye.

Then, the fallout.

She has no friends.

...

The alcohol incident blows over quickly.

Rufus, usually a father who enjoys reprimanding his kids for past mistakes, becomes an Upper East Side parent.

They never talk about it, but the unspoken agreement seems to be that he tolerates her binge drinking as long as she goes to school and never causes a scene.

She doesn't want to know what Lily told him to make this happen.

...

Turning to Chuck when she has no one left to turn to seems like the logical conclusion to a terrible year for Jenny Humphrey.

He was there, back at the Kiss on the Lips party, when she felt like an outsider who had no one. Now, two years later, she still feels like she has no one, but this time around it might just be true.

They use each other.

It's one of the many unspoken agreements of the Upper East Side, this routine they fall into. She knocks on his suite door and he lets her in, pours them some scotch to go with the exhausted looks on their faces.

She wonders why he lets her in the first time it happens before realizing that he, too, must feel alone. Bart is dead, Blair is off chasing royalty and Nate and Chuck have long stopped being best friends.

It's a couple of weeks into their blossoming union as the lonely alcoholics community (their slogan: _If one member suffers, all suffer together; if one member is honored, all rejoice together;_ they found it on a bible app one night after four glasses of Glenn McKenna) when he introduces her to his dealer – or dealer_s_; they're a team - a guy named Chris, who looks more like a lawyer than a sketchy drug dealer (he's the supplier, doesn't actually do the dirty work himself) and Marc, a tall guy who looks like you shouldn't mess with him unless you want a knife in your chest.

The guys are all right, easy company to keep without having to try. She can see why Chuck hangs out with them. They're drug dealers, they have no reason or the necessary moral high ground to judge you for anything.

...

She takes Ecstasy, just once, and finds she likes it a little.

The level of confidence she feels is one she's never experienced, the sad truth of her lonely existence forgotten for a while.

She laughs, dances and feels like the world revolves around her.

The knock on the suite door makes her jump up. She grabs Marc's hand in the process and drags him with her as she runs towards the door in excitement. He's running too, and gets there before she does.

Marc opens the door and grins at the person in front of him. Jenny comes crashing against him, hands grabbing his hips, just as she hears him greet their guest.

"Nate! Hey, man! Haven't seen you in ages." It must be an unexpected turn of events for Nate, if his forehead, wrinkled in confusion, is any indication. He's carrying a large duffel bag.

She doesn't care, she's just happy to see him.

Jenny giggles, steps in front of Marc and throws her arms around Nate.

"You're here!" She nearly knocks them both off balance; Nate just barely manages to steady himself on the wall next to the door.

Once he's back safely on both feet, he pushes her away roughly, holding her at arms length as he looks at her closely.

"I must have missed the Gossip Girl blast about you getting fucked up on E with Chuck and his dealers."

She rolls her eyes and laughs.

"Stop being so serious! Come in, let loose and dance with me!"

Her attempt to pull him further into the room is met with resistance.

"Stop it! What the hell is wrong with you, Jenny?" Before she can respond, she feels a hand on her hip and looks to her right to see Chuck standing next to her. "You're embarrassing yourself", Nate adds.

"Nate." Chuck says, voice stern, not taking his eyes off of him. "Back off."

She wonders when Chuck became the guy who protects her. A glance in his direction makes her smile again – he looks like he's about to get mad.

"Really Chuck? Drugging your own stepsister to take advantage of her is twisted, even for you."

Without hesitation, Chuck takes a step forward and pushes Nate out the door.

"You should go."

She hears Nate give a defeated laugh before Chuck closes the door in his face.

...

The night Jenny sleeps with Chuck Bass is filled with ecstasy. (In every sense of the word)

The morning after she arrives home to find Rufus leaning at the kitchen counter, looking at her like she's some sort of monstrosity.

"What's wrong?"

The question escapes her before she can stop herself. She doesn't want to have a conversation right now, all she wants is to go to her room and give into the feeling of exhaustion (both mentally and physically) that she's experiencing.

"I know."

She sighs. The last thing she needs is a guessing game. It's 11 AM and she hasn't slept yet.

"You know what, dad? Be specific."

"I'm surprised you don't know what I'm talking about. Dan showed me the Gossip Girl blast. Drugs, Jenny, really? And Chuck, of all people? Do you have any idea how much trouble you're in?"

He's caught her off guard.

Without looking back, Jenny walks to her room and locks the door.

...

That seals it. Boarding school in New England, an idea no doubt planted in Rufus' head by Lily.

(She hears them talk about it one night – "It did wonders for Serena! I'm telling you Rufus, this is the right thing to do.")

Her flight is set for three days later and she has strict instructions to not leave her room during those three days unless it's deemed absolutely necessary by either Rufus or Lily first.

So basically, she's really bored. There's only so much TV you can watch.

A blast about her brother punching Chuck makes her laugh for the first time in days, and she decides to text Chuck to laugh at their shared misfortune.

Neither of them even remotely believes that the other could harbor romantic feelings for them so they slip back into sarcasm filled conversation immediately.

_Heard you got punched today… _She has to smile at the mental image of her brother punching Chuck, of all people.

_Have fun at boarding school_, is his response.

She smirks. _Very funny, Chuck._

_Bored yet? _Is his immediate reply.

_Do you even have to ask? _She makes sure to include a frustrated looking emoticon, because she knows how much he hates those.

_Want me to come over for family dinner? _

The very idea of a shared family dinner is enough to make her crack up.

She's glad their friendship hasn't changed.

_We could always pretend I'm pregnant…_

She's sure even Chuck laughed at that one.

...

It's strange, being at the same boarding school Serena went to.

She finds that she has a reputation at the school before she's even unpacked. Apparently even the small community of Waverly Academy reads Gossip Girl.

But still, it's a new beginning and it doesn't feel as bad as Jenny expected it to. The campus is gorgeous and the people are decent.

(Most of them, anyway. There's that Callie girl from Georgia who spreads rumors about Jenny being a stripper, but Jenny ignores her as best as she can.)

It stops feeling like a punishment the day she finds out there are numerous fashion classes she can take.

...

Nate calls her two days after she arrives.

It's the single most awkward conversation she has ever had to have.

She apologizes for how she attacked him at Chuck's while he just makes noncommittal noises.

Awkward silence ensues.

"You sound better." He says, finally. "Well, I just wanted to wish you good luck at boarding school." She wonders if she can hear a hint of a smile in his voice.

"Thanks", she says, though she doubts that's the reason he called.

They both know the conversation is over now so she mumbles "Bye" and hangs up first. The feeling she's left with is one she can't fully comprehend.

Maybe someday they'll go back to being friends.

Maybe someday she'll go back to New York and things will be simpler.

...

Boarding School is just the beginning to her travels.

The summer before her senior year she spends in London at an internship with an incredible up-and-coming designer.

The summer after, she moves to London for good.

She's evolved, doesn't question her past decisions anymore.

There's a price to pay for acceptance on the Upper East Side, she knows that now and she's not willing to pay it.

...

It's the invitation to _ChuckandBla_ir's wedding that brings her back to New York after successfully avoiding it for four years. (She's been in the city a couple of times for business over the years but she's successfully avoided _her_ New York and the people that includes.)

Her and Chuck haven't been in touch since he was in London on business two years ago. Immediately she knows that she has to go, even feels like she just might _want_ to.

Besides, she feels ready to face the wrath of her family.

(And even if she didn't, she wouldn't miss this – it's _ChuckandBlair _- the epic conclusion.)

It works out perfectly – she has to fly in for a fitting of an upcoming small line she designed anyway – so she really has no excuse not to go.

(And okay, she will admit that she's curious to see how things have changed.)

Everybody is surprisingly nice to her. Her dad acts as though nothing happened – doesn't even mention the fact that she hasn't bothered to visit them the past few years.

Chuck makes some snarky comment about how he thought she died and she just laughs, shakes her head and hugs him. Then she hugs Blair, who looks both surprisingly relaxed and happy. She looks at them for a moment and laughs. They're such an unlikely couple, but they make so much sense. Before either of them can move away, she hugs both of them at the same time and wishes them all the best.

"Welcome to the family!" She tells Blair, who laughs and tells her to not expect her to attend any family waffle brunches. Blair is hurried away by an excited tall blonde bridesmaid - Jenny thinks it might be Serena but the "hi" the blonde throws her way is so quick that she can't be sure – before she can catch Jenny's response. "I wouldn't go either, if I were you."

It all goes by in a blur and before she knows it, she's sitting in front of her plate of chicken. She's the first one to sit down and she quickly scans the place cards around the table to prepare for the conversations to come.

Of course Chuck made sure to sit her at the important table – besides bride and groom, both maid of honor and best man will be there with her. She's not sure if she should be thankful or resentful, but at least she won't have to sit through dinner with her dad and Lily this way.

Nate sits down next to her and she mentally curses Chuck.

"Hey", he says, as he looks her up and down. "Wow." A smile forms on his lips.

Jenny laughs. "Like the dress?"

She feels more confident, talking to him now. Finding herself has done wonders for her confidence.

"That too. Just shocked to see that you're actually here."

"I'm guessing from your facial expression that this is the good kind of shock", she deadpans as she reaches for her champagne flute.

"Yeah, I guess so", he smiles. Before they can continue their conversation, Chuck, Blair and Serena sit down at their table. They share a few glances during the speeches from Lily and Serena and she's pretty sure she laughs the loudest when Nate starts his speech with the statement that there were many obstacles that Chuck and Blair had to overcome – for example him.

She's always loved the kind of inappropriate (but true) things that you only ever get to say during speeches at weddings.

...

"How long are you in town for?" He asks her at the end of the night as they share a dance that she reluctantly agreed to after he used his very convincing fake pout.

"A few days", she replies as casually as she can, given the fact that she knows he'll ask her to hang out with him now.

He smiles and squeezes her hip where he's holding it.

"Any chance you might have time for some lunch tomorrow?" When she doesn't answer immediately, he keeps talking. "I mean, somebody needs to fill you in on all the gossip you missed now that Gossip Girl doesn't blog anymore."

She laughs. "Fair enough."

_..._

_It was bound to happen_, she tells herself as she makes the final preparations to move the headquarters of Jenny Humphrey designs to New York.

She finally feels like she belongs here now, finally thinks she has the support from family and friends that she needs to lead a happy life in the city where, ten years ago, she felt like a fool.

Life is good to her at last.


End file.
